Global Patent Index - EP 4008735 A1

EP 4008735 A1 20220608 - NON-IONIC BLOCK COPOLYMERS AND PHARMACEUTICAL COMPOSITIONS DERIVED THEREFROM

Title (en)

NON-IONIC BLOCK COPOLYMERS AND PHARMACEUTICAL COMPOSITIONS DERIVED THEREFROM

Title (de)

NICHTIONISCHE BLOCKCOPOLYMERE UND DAVON ABGELEITETE PHARMAZEUTISCHE ZUSAMMENSETZUNGEN

Title (fr)

COPOLYMÈRES SÉQUENCÉS NON IONIQUES ET COMPOSITIONS PHARMACEUTIQUES DÉRIVÉES DE CEUX-CI

Publication

EP 4008735 A1 20220608 (EN)

Application

EP 22154117 A 20180329

Priority

  • GB 201705287 A 20170331
  • US 201762479582 P 20170331
  • EP 18777331 A 20180329
  • CA 2018050399 W 20180329

Abstract (en)

PVP-PLA block copolymers as defined in Formula I:wherein, x is an initiator alcohol having a boiling point greater than 145°C, n is, on average, from 20 and 40, and m is, on average, from 10 and 40, wherein the block copolymers have a number average molecular weight (M<sub>n</sub>) of at least 3000 Da. Polymers demonstrating flexibility in formulating multiple low-solubility active pharmaceutical ingredients (APIs) are described. Liquid and dry pharmaceutical formulations comprising an API are described, along with delivery methods, uses, and kits. APIs may include, e.g. flurbiprofen, celecoxib, acetaminophen, or propofol. Also provided is a method of synthesizing the PVP-PLA block copolymers by (i) initiating polymerization of D,L-Lactide from the initiator alcohol x to form poly(lactic acid), adding a xanthate to form a PLA macroinitiator, and polymerizing NVP onto the PLA macroinitiator, by controlled polymerization, to form the block copolymer compound of Formula I.

IPC 8 full level

C08F 290/06 (2006.01); A61K 9/14 (2006.01); A61K 31/05 (2006.01); A61K 31/167 (2006.01); A61K 31/192 (2006.01); A61K 31/635 (2006.01); A61K 47/34 (2017.01); C07C 39/06 (2006.01); C07C 57/38 (2006.01); C07C 233/25 (2006.01); C07D 231/12 (2006.01)

CPC (source: EP GB US)

A61K 9/00 (2013.01 - GB); A61K 9/1075 (2013.01 - EP US); A61K 9/5192 (2013.01 - US); A61K 31/05 (2013.01 - EP US); A61K 31/167 (2013.01 - EP US); A61K 31/192 (2013.01 - EP US); A61K 31/415 (2013.01 - EP US); A61K 47/32 (2013.01 - EP); A61K 47/34 (2013.01 - EP US); C08F 226/10 (2013.01 - GB); C08F 299/04 (2013.01 - GB); C08G 63/08 (2013.01 - GB); C08G 63/6882 (2013.01 - EP); C08L 39/06 (2013.01 - GB); C08L 67/04 (2013.01 - GB); C08L 87/005 (2013.01 - EP); A61K 9/19 (2013.01 - EP); C08G 2261/126 (2013.01 - EP GB)

Citation (applicant)

  • KAZUNARI MASUTANIYOSHIHARU KIMURA: "From the Monomer to the Polymer", 2015, THE ROYAL SOCIETY OF CHEMISTRY, article "PLA Synthesis", pages: 1 - 36
  • ANN-CHRISTINE ALBERTSSONINDRA K. VERMA: "Recent Development in Ring Opening Polymerization of Lactones for Biomedical Applications", BIOMACROMOLECULES, vol. 4, 2003, pages 1466 - 1486, XP009123105, DOI: 10.1021/bm034247a
  • IRENE BARTOLOZZIROBERTO SOLAROETIENNE SCHACHTEMO CHIELLINI: "Hydroxyl end-capped macromers of N-vinyl-2-pyrrolidinone as precursors of amphiphilic block copolymers", EUROPEAN POLYMER JOURNAL, vol. 43, 2007, pages 4628 - 4638, XP022318818, DOI: 10.1016/j.eurpolymj.2007.08.011
  • LIONEL DELAUDEMORGAN HANSSOMENATH CHOWDHURY: "Microwave-Assisted Synthesis of the 1,3-Dimesitylimidazolinium Chloride", ORG. SYNTH., vol. 87, 2010, pages 77 - 87
  • LEI XIONGHONG WEI: "JiangAffiliated withSouth China University of Technology, Di Zhen Wang, Synthesis, characterization and degradation of poly(dl-lactide)-block-polyvinylpyrrolidone-block-poly(dl-lactide) copolymers", JOURNAL OF POLYMER RESEARCH, vol. 16, 2009, pages 191 - 197
  • KM PARKCK KIM: "Preparation and evaluation of flurbiprofen-loaded microemulsion for parenteral delivery", INTL J PHARMACEUTICS, vol. 181, 1999, pages 173 - 179, XP055007325, DOI: 10.1016/S0378-5173(99)00029-0
  • RD KNIHINICKIRO DAYGG GRAHAMKM WILLIAMS: "Stereoselective disposition of ibuprofen and flurbiprofen in rats", CHIRALITY, vol. 2, 1990, pages 134 - 140
  • SZPUNAR, G. J.ALBERT, K. S.BOLE, G. G.DREYFUS, J. N.LOCKWOOD, G. F.WAGNER, J. G.: "Pharmacokinetics of flurbiprofen in man. I. Area/dose relationships", BIOPHARM. DRUG DISPOS., vol. 8, 1987, pages 273 - 283
  • CEFALI, E. A.POYNOR, W. J.SICA, DCOX, S.: "Pharmacokinetic Comparison of Flurbiprofen in End-Stage Renal Disease Subjects and Subjects with Normal Renal Function", JOURNAL OF CLINICAL PHARMA, vol. 31, 1991, pages 808 - 814
  • TABURET, A. M.SINGLAS, E.GLASS, R. C.THOMAS, F.LEUTENEGGER, E.: "Pharmacokinetic comparison of oral and local action transcutaneous flurbiprofen in healthy volunteers", JOURNAL OF CLINICAL PHARMACY AND THERAPEUTICS, vol. 20, 1995, pages 101 - 107
  • QAYYUM, A.NAJMI, M. H.FAROOQI, Z-R: "Determination of Pharmacokinetics of Flurbiprofen in Pakistani Population Using Modified HPLC Method", J. CHROMATOGR. SCI., vol. 49, 2011, pages 108 - 113
  • KAISER DGBROOKS CDLOMEN PL: "Pharmacokinetics of flurbiprofen", AM. J. MED., vol. 80, no. 3A, 1986, pages 10 - 5, XP023305073, DOI: 10.1016/0002-9343(86)90104-X

Citation (search report)

  • [Y] WO 2011130834 A1 20111027 - LABOPHARM INC [CA], et al
  • [Y] CA 2547938 A1 20050616 - LABOPHARM INC [CA]
  • [XY] K. RAMESH ET AL: "Synthesis of well-defined amphiphilic poly(d,l-lactide)-b-poly(N-vinylpyrrolidone) block copolymers using ROP and xanthate-mediated RAFT polymerization", POLYMER, vol. 53, no. 25, 11 October 2012 (2012-10-11), GB, pages 5743 - 5753, XP055540591, ISSN: 0032-3861, DOI: 10.1016/j.polymer.2012.10.009
  • [Y] F. RAVENELLE ET AL: "Anaesthetic effects of propofol polymeric micelle: a novel water soluble propofol formulation", BRITISH JOURNAL OF ANAESTHESIA., vol. 101, no. 2, 11 June 2008 (2008-06-11), GB, pages 186 - 193, XP055540596, ISSN: 0007-0912, DOI: 10.1093/bja/aen147
  • [Y] LE GARREC D ET AL: "Poly(N-vinylpyrrolidone)-block-poly(d,l-lactide) as a new polymeric solubilizer for hydrophobic anticancer drugs: in vitro and in vivo evaluation", JOURNAL OF CONTROLLED RELEASE, ELSEVIER, AMSTERDAM, NL, vol. 99, no. 1, 14 September 2004 (2004-09-14), pages 83 - 101, XP004549072, ISSN: 0168-3659, DOI: 10.1016/J.JCONREL.2004.06.018
  • [Y] LUO L ET AL: "Novel Amphiphilic Diblock Copolymer of Low Molecular Weight Poly(N-vinylpyrrolidone)-block-poly(D,L-lactide): Synthesis, Characterization, and Micellization", MACROMOLECULES, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, UNITED STATES, vol. 37, no. 11, 1 June 2004 (2004-06-01), pages 4008 - 4013, XP008111990, ISSN: 0024-9297, [retrieved on 20040504], DOI: 10.1021/MA035910Q

Designated contracting state (EPC)

AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO PL PT RO RS SE SI SK SM TR

DOCDB simple family (publication)

GB 201705287 D0 20170517; GB 2561009 A 20181003; GB 2561009 B 20200513; CA 3054981 A1 20181004; EP 3601392 A1 20200205; EP 3601392 A4 20201202; EP 3601392 B1 20220309; EP 4008735 A1 20220608; ES 2910378 T3 20220512; PT 3601392 T 20220414; US 11266741 B2 20220308; US 2021322556 A1 20211021; US 2022152208 A1 20220519; WO 2018176158 A1 20181004

DOCDB simple family (application)

GB 201705287 A 20170331; CA 2018050399 W 20180329; CA 3054981 A 20180329; EP 18777331 A 20180329; EP 22154117 A 20180329; ES 18777331 T 20180329; PT 18777331 T 20180329; US 201816497925 A 20180329; US 202217591241 A 20220202